1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → Tert-butyl 4-(methylthio)piperidine-1-carboxylate

HRID 350717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350717
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[Na].[CH3:20][SH:21]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH3:20][S:21][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

Komponenten

5

Edukt 2

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 45051789Methylmercaptan sodium

Produkt 1

HCID 11053478Tert-butyl 4-(methylthio)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 4-(methylsulfonyl)oxypiperidine-1-carboxylate (12.5 g), methylmercaptan sodium salt (3.31 g), tetra-n-butylammonium iodide (1.66 g) and tetrahydrofuran (50 mL) was stirred at room temperature for 72 hrs. The insoluble material was filtered through celite and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and tert-butyl 4-(methylthio)piperidine-1-carboxylate was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio) (6.89 g, yield 67%).

Aufarbeitung

  1. filtrationThe insoluble material was filtered through celite
  2. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-5c841c5f7ea6479d82cc695701509b8b
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183276B2

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